Women Dating Over 50: Are We in No-man’s Land?


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By Jackie Pilossoph, Divorced Girl Smiling Editor-in-Chief

Jackie, I am approaching 50, and just over one year separated from my husband. As I look forward and begin to think about the possibility of future relationships, I can see that dating over 50 might be difficult.

I notice that lots of people who were married for maybe 10 years or less seem to say…we got married early, found out it didn’t work, and then later remarried and have found long term, happiness with their next partner/spouse. What I also notice is that I don’t seem to hear any/as many happy stories about people (like me) who were married 20-25 years, got divorced, and then found happiness/ marriage, etc again.

It seems to me that lots of middle aged women get divorced and stay single. I might just be feeling sorry for myself but it seems to me that a 50ish woman is somewhere in no-man’s land for a future relationship. I may be generalizing but do you see the same thing?

Let’s face it. Men our ago want to meet someone younger. Younger guys aren’t a great fit. And, older men have interest but that isn’t really fair either. Maybe fair isn’t the right word. I would like to know your thoughts on the likelihood of 50 year old women finding a second life partner. Especially one in the same age bracket.

It’s really funny that I would get this email from you, wondering about dating over 50. Why? Because I’m turning 50 in 6 months, and I’m recently single again.

So, I guess what I’m trying to say in response to your asking my thoughts on the likelihood of a 50 year old woman finding a second life partner is: I HAVE NO CLUE, I’ll let you know when I find out? LOL!

I do have a few things to say about your email. The first is in regards to no-man’s land. I have always believed that 50’s is in fact, no-man’s land, whether you are single, married, divorced or widowed, the reason being that you aren’t really young anymore, but you aren’t old either.

I have had some issues while shopping for clothes in recent years, because all the clothing out there either seems too young or too old for me. Perhaps this same attitude applies when it comes to dating. If in your 40’s, it seems OK to me to date guys in their 30’s, 40’s or 50’s. But 50 is a different story. Guys in their 30’s are definitely out, guys in the 40’s might work, but they might want women in their 30’s or 40’s, guys in their 50’s definitely want girls in their 30’s or 40’s, and guys in their 60’s are just too old. (no offense.)

So, what to do? Being new at this, I’m going to go for just being my Gosh darn self and if someone wants to date me, great, and if they think I’m too old, then so be it. It’s all about believing you have a lot to offer someone, which I do. Am I perfect? Hell no. Am I kind of old? Yep. But that is what it is. I am me and all I can do is live life to my potential. And that’s what I’m doing.

Also, consider a wide age range when dating. I think as people get older, age matters less. So, not only does a large age range, (let’s say 42-57 perhaps?) increase the number of potential men for you, but I think you will see that age is only a number, unlike it was, say if you were 30, dating a 20 year old.

The thing that bothered me most about your email is this part:

What I also notice is that I don’t seem to hear any/as many happy stories about people (like me) who were married 20-25 years, got divorced, and then found happiness/ marriage, etc again.

You write: “found happiness/marriage etc. again.” The slash between happiness and marriage clearly indicates that you equate happiness and marriage, and that’s something I definitely don’t do. I equate happiness with: children, family, career, fun and surrounding myself with people I love and enjoy, whether that involves romantic love or not.

My bottom line is, I just want to be happy. I don’t have to be married for that to happen. I would ultimately like to be married again (I think) but anyone who reads this blog should know by now that I don’t feel marriage brings happiness unless you wait for the right person and/or the right time.

The last thing I will tell you to do is to slow down and don’t panic. Separated for one year is a very short time. Work on yourself. Work on healing. Have fun. Go on dates, but don’t force the serious relationship. Let it just happen.

Remember, 50 is the new 30! Is that cheesy? Who cares. I believe it!

I’ll leave you with this–Beautiful women who are over 50:

Michelle Pfeiffer, Andie MacDowell, Catherine Keener, Oprah, Madonna, Kim Basinger, Kim Catrall, Christie Brinkley, Diane Sawyer, Jennifer Grey

Best of luck!

Divorced Girl Smiling, a novel by Jackie Pilossoph

Free Gift With Purchase, a novel by Jackie Pilossoph


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Author: Jackie Pilossoph

Divorced Girl Smiling offers advice, inspiration and hugs. If you want a Cinderella story, be your own fairy godmother. You're the only one who can pick out that perfect glass slipper!

30 Responses to “Women Dating Over 50: Are We in No-man’s Land?”

  1. darmok

    I enjoyed your article too for many reasons. I left my wife after 25 years of marriage and 30 of being together. I could think of many reason but I had lost happiness a long time ago and tried to hold on. I didn’t tell her what I was feeling for so many years and just felt it was my duty to be a good husband, father, and christian, don’t worry about how I felt. Eventually I asked for a divorce and it devastated my wife. Choosing between making everyone else happy or yourself, including God, was a huge decision for me, I decided I needed to be happy. I am 58 and thought about living my remaining years up happy and just could not bare the thoght. A lot of people have their opinion on what I did and I am sure some, if not most, think I am a monster for doing this after so many years. I do have some guilt, guilt, for not letting my ex-wife know what I was thinking or what I was feeling. I do not think it would have made a difference bhe will never believe that. Anyway, I hope this is not true, women over 50 divorced never finding happiness again. I loved your statement of marriage not making you happy. I know it will take my ex years to get over our divorce, but I do wish her the best, sometimes more than what I wish for myself. I keep hearing people say it is easier for men to get over a divorce than women, hopefully not too true. I wish my ex would read your blog. We can talk sometimes but often it goes back to what I did to her and that is not a good place to be, ever. Thanks

    Reply
    • Susan

      You’re a self-centered jerk. I agree with Nancy. You should have left your wife years ago so she could have found someone deserving of her. Men like you make me sick to my stomach. I hope you reap what you’ve sown.

      Reply
    • Priya Jay

      Namaste. Your Divorce Journey is yours alone to take. If this woman was dragging you down, you owed it to yourself to begin your Eat, Pray, Love Journey.

      So glad you chose the right path, just as so many women have when their male counterparts began to become a burden on their paths to self-realization.

      Reply
  2. nancy

    darmok, you would have done your wife a ig favour had you left her many years before you did. that way, you would have given her the gift of the chance to find real love in an honest relationship and you as well could have gone on with your life.

    Reply
  3. LaLaverneLa

    you would have done yourself and your wife a favor if you had spoken with her about your feelings. You did a large disservice to your relationship by just walking out with no reason other than you are not “happy”, before leaving you could have undergone counselling either on your own or as a couple. You dont mention if you have children and how they feel about what you have done, or if you still have a relationship with them. You were exceptionally selfish and i suspect you may have other issues at play. I wonder if you are any “happier” now being on your own? or if you just enjoy not having any responsibiities to anyone else? What you did was a callous cop out and the karma bus will kick you in the ass sooner or later.

    Reply
  4. Sherrie lee Cormier

    Im a 50 yr old Private Home care worker for the last 6 plus years love my job.I have Older children and 4 rescue cats. I work long hard hours with little time to socialize so Im looking for someone who wont waste my time . I love adventures and travel and the simple picnics in the back yatrd..im passionate and can cook and make blanket forts to read stories im fun and loyal and nuturing and Ive so much love left to give to someone with ambition and drive for a future together ..Im saving my last first kiss just for him!

    Reply
  5. Jeff

    I’m a man , 53 , my 23 year marriage ended in 2010. Women my age have so much more to offer . Most have a real sense of who they are and what they want in a relationship . They’re open and dedicated to the making this next part of their lives really amazing! They come to life .. revel in the freedom that comes with being single with so much waiting to be discovered.
    Some men are genuinely drawn to a younger woman’s energy but from what i’ve seen most are looking for an ego boost.
    To all you women who might be wondering what this next stage holds… go out there and enjoy life , your radiance will be more than enough to attract real men.

    Reply
    • Jackie Pilossoph

      I LOVE you!! This is so wonderful for women to hear because most of them don’t believe this. Thank you!

      Reply
  6. Tammy Kovach

    My husband of 28 years recently left me. He tried to say it was because I am moody but I am happy and easy going. I never get stresse, sad or angry and absolutely never yell at anyone. I found out two weeks ago he is having an affair with a nurse’s aide from the nursing home where his mother was a resident until she passed in December. I am still trying to process this. 6 years ago he did also went to stay with his sister and had an affair with an old friend from high school. She ended it and he begged to come home. I let him and now here we are again. The thought of being single terrifies me. I am in decent shape and average looks but feel like a duck out of water. I still have a divorce ahead of me but would like to keep busy so I don’t miss our old life or him. Not sure what to do but go to the gym and meet girlfriends occasionally. Also spend time with our 21 year old twins when they are not busy with work or school. I don’t want them worrying about me.

    Reply
    • Jackie Pilossoph

      I am so sorry that you are going through this. A couple things. Don’t ever say your looks are “average” or that you are “decent.” You will find that over 50, everyone is semi-old and out of shape, but we do the best with what we have, and the focus is on health, how you feel-your energy, how you live your life, inner beauty, and being happy.You are going to do great. Your self-description of “happy, easy going, not stressed and never yell” is wonderful! Stay that way! Take one day at a time. xo

      Reply
  7. Cindy

    My husband and I have not been in a marriage for over 20 years. I could not fix it and we live together until he is out of law school (his way or nothing). I am finally dating since I have forgiven and moved on emotionally. It is tough out there and I some how am meeting angry men who are not the least emotionally available. It has been depressing meeting men who are so angry about the world, from being underemployed, angry at the women they meet and generally unpleasant. Sometimes when I explain that I work, have activities that I engage in and still have children in my home they are mad at me. I thought men wanted a woman who has her own money and life. I don’t understand dating men at 50.

    Reply
  8. BillyG

    I am totally stumped, Im 55yo guy seeking lady 50 to 60, why are women even picky at this age ??

    Reply
    • Been there

      “why are women even picky at this age ??” That says it all about why you can’t get a woman interested in you, no one wants a man who has such contempt for them. What do you bring to the table? Did you even consider the unlucky women who’ve been subjected to your bad attitude have to be getting something out of it?

      Mature women are established and independent, just because they’re over 50 doesn’t mean they are going to put up with someone who will mistreat them, if anything they have even less of a need for men now they’re done with babies.

      Reply
    • Maria NK

      I am way more picky in my 50s then I was in my 20s. There was not much to loose back then. After I have built the life I love, based on my values, making my own decisions – it has to be someone really special to make it worth to change it again. Most women in their 50s don’t just want anybody, and many men are confused about that. We are picky, because we can do better, with or without a man.

      Reply
  9. Been there

    In spite of the rhetoric about older women being unlucky in love the feedback Ive been getting from women over 50 its the women who reject the men, not that the single men over 50 are necassarily catches, however I dont see good men suddenly going bad due to age or divorce, I tend to think they were bad the whole time and now they’re just nastier and more vocal, it’s like age has revealed what was always there, the gloves might be off but so are the masks.

    Many divorced women are once bitten when it comes to entering into another long term commitment, they found they’d been saddled with a lot of the work when they were married and being single again was a relief, they use the time between empty nest (spare time and money) and menopause (which can be rocky for some women) as an opportunity to find who they are and what they want out of life having spent so many years subverting that part of themselves to care for others (which a lot of men expect women to do throughout their liferime and call them “selfish” if they dare to have autonomy), it’s a brief window and you should grab it with both hands. A holiday fling might not be a bad idea either if the opportunity comes up, other than that something to get back in touch with your sensual side like pole dance classes or some other cheesy sounding women centred classes, they can be a lot of fun.

    That being said if you enjoyed being married and are keen to do it again as long as you’re social and mixing with people on the same level as you (not online dating or the singles scene, they’re both cespits) I can see no reason why you wouldn’t meet some great guys who are also looking for the same thing. The field is a little thinner due to people going out less as they get older and diversified interests (at 50 a Saturday night at the club isn’t really something that appeals like it did in your 20-30s) but you might ght be surprised just how much interest their is and who from. I wouldn’t rule out younger men either, as long as the age difference isnt uncomfortably obvious and your bith have the same goals lots make great husbands.

    Reply
  10. Marie

    My mother is almost 60. She’s been single for about 8 years now. I know it’s because she’s nervous about dating (also, my brother and I try not to be SO protective of her…As hard as that is), but I know she’s lonely. It breaks my heart knowing that I can’t do anything about it. Any advice on how to cure the loneliness? She keeps very busy, but it isn’t enough. I just want to help her, but I don’t know how.

    Reply
  11. Byron

    “…I just want to be happy. I don’t have to be married for that to happen.” And there’s the key – or maybe the challenge to all of us?

    In the few months since my divorce was final, I’ve been more open to meeting some of the (single) women I see frequently. I’m not dating mind you, I’m not ready for that. But being social, enjoying some conversation, getting to know new people, … It’s kind of therapeutic. I’m 52. They range in age from 34 to 53. They all have a story, some have a lot of baggage they carry around – just like I do. And I do even find a couple of them “attractive.” But not in any physical sense, or having anything to do with their age. They laugh. They’re funny. They’re confident. They don’t need anyone to “rescue” them.

    I’m attracted to them because THEY’RE … JUST … HAPPY.

    They’re not happy BECAUSE they go to the gym, or BECAUSE they started a new hobby, BECAUSE they found a great new job, and certainly not BECAUSE of anything to do with my presence in their lives. They’re happy because, regardless of how it is that they’ve landed where they are, or what they’re doing at the moment, they take it all in stride and find a way to make the best of it. They have this, and everyone around them eventually knows it.

    On the other hand, there are the sad ones. Woe is me. The “wish I could find a guy” ones. Those whose biological clocks tick so loudly that you get headaches listening. While I feel bad for them, I have a feeling that I know now why things aren’t happening the way they’d like? I was married to one of those, and I realize now that most of the women I dated prior to that had an air of desperation around them as well. Never again.

    Don’t focus on your age. Focus on yourself. BE yourself. Learn to be the master (or mistress) of your own happiness. No, it may not help YOU find that special someone, but it might help THEM find you!

    Reply
  12. PA Brook

    I found out quickly after being divorced in my mid 50s both from myself and from the women I dated. Things are different at this age. When we are first timers, we all have the same goal. Career, get married, buy a house, have rug rats. There are a LOT of people available who have the same goal. I know I fell in love quickly and easily back then. I’m not saying it was easy to find the right person, just easier. That person is the “Who” in our life.

    Now something else has creeped into the equation. We have been free for a while, have our own life which is important and now we want to find someone. Preferably to fit into our lifestyle. That’s the rub. That lifestyle at this age is much more important to us than when we were first hunting for happiness in our 20s. Not only do we need to find the right person (the “Who”), we need to find someone who has the same desires in a relationship. It’s the “What” in our life.

    The What is the type of relationship you want. It includes what you do, how often you see each other, or if you like to do the same things. Do you stay at home or go out? Do you go to the movies or go dancing? Do you hang out with each other when you are doing nothing? Does one want to play scrabble while the other is glued to HGTV? You get the point. A critical aspect of the What is how often you each want to see the other. Not how often you see each other, how often you want to. The difference is huge.

    I have met many Whos but only a few compatible Whats. Finding the right combination has proved daunting. But it is doable if you understand and recognize the difference.

    One final thought. If you have a list of Must Haves (thank you eHarmony), make sure they really matter. Most of them are Must Haves because you don’t have a Who. Think about what is really important to you. And be open to new ways of doing things. Good luck! http://bit.ly/2bHSitu

    Reply
  13. Louis cypher

    Most men who divorce trade in their wives/long term partner do so because they met someone else who they fancy more because the new woman is better looking/ in better shape/ doesnt moan as much/is a breadth of fresh air/or a no of other things. Go Figure

    Reply
  14. Tina

    I am women that is 55 years of age. I love the positivity of this blog. Be your own special self is the best advice I have ever received. I would love to meet a man who fits in my life, but if that doesn’t happen I am good. Just give yourself time to heal, don’t jump into another relationship because you can’t be alone. Do what makes you happy, your soul will appreciate this.

    Reply

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